Free accessResearch articleFirst published online 2013-7
Synthesis of a Key Intermediate,10-Acetyl-7-( t -butyldiphenylsilyloxymethyl)-4-methylbicyclo[5.3.0]dec-4-en-1-ol,in the Synthesis of Pseudolaric Acid A
10-Acetyl-7-(t-butyldiphenylsilyloxymethyl)-4-methylbicyclo[5.3.0]dec-4-en-1-ol was synthesized by aldol cyclization to a five-membered ring, epoxidation, samarium diiodide-induced ring opening, and the RCM reaction to the seven-membered carbocycle. This method has succeeded in constructing the desired stereochemistry in the synthesis of pseudolaric acid A.
NakashimaK, InoueK, SonoM, ToriM., (2002) Total synthesis and absolute configuration of liverwort diterpenes, (-)-13(15)E,16E-3p,4p-epoxy-18-hydroxysphenoloba-13(15),16-diene and (-)-13(15)Z,16E-3p,4p-epoxy-18-hydroxysphenoloba-13(15),16-diene by use of ring closing metathesis reaction applied to seven-membered carbocycles with tri-substituted double bond. Journal of Organic Chemistry, 67, 6034–6040.
2.
ProfittJA, WattDS, CoreyEJ. (1975) A reagent for the a,p reduction of conjugated nitriles. Journal of Organic Chemistry, 40, 127–128.
